Dithiopentacene derivatives, their preparation and the use thereof as electron acceptors in charge transfer complexes
AssigneeCiba-Geigy Corporation
InventorPeter Chetcuti
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Abstract
The present invention relates to novel dithiopentacene derivatives, to a process for their preparation, to charge transfer complexes obtained from said dithiopentacene derivatives as electron acceptors and unsubstituted or substituted ferrocene, chalcogenated fulvalenes or aromatic nitrogen compounds as electron donors. The invention further relates to a process for their preparation; to compositions comprising a plastics material and such a CT complex; and to the use of said CT complexes as electrical conductors, conveniently for the production of electrically conductive films, foils or coatings.
Claims31
A charge-transfer complex of formula II
- [(A).sub.p ].sup.q.crclbar. B.sup.q.sym. (II)
- wherein
- a) A is the radical anion of a compound of formula I or of a mixture of compounds of formula I ##STR6## wherein the R substituents are identical and are H or C.sub.1 -C.sub.4 alkyl, the adjacent R substituents, taken together, are --(CH.sub.2).sub.3 -- or --(CH.sub.2).sub.4 --;
- R.sub.1 is H or C.sub.1 -C.sub.4 alkyl;
- and X.sub.1 is .dbd.N--CN, and X.sub.2, X.sub.3 X.sub.4 are .dbd.O or .dbd.N--CN, and
- b) p and q are 1, and
- B is the monovalent radical cation of a compound of formula IIIa or IIIb ##STR7## wherein R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are each independently of one another H, linear or branched C.sub.1 -C.sub.18 alkyl-(Z.sub.1).sub.n --, phenyl-(Z.sub.1).sub.n -- or benzyl-(Z.sub.1).sub.n -- which are unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio, or R.sub.2 and R.sub.3 as well as R.sub.4 and R.sub.5 are each independently of the other trimethylene, tetramethylene, --Z.sub.2 --(CH.sub.2)--Z.sub.2 --, --Z.sub.2 --(CH.sub.2).sub.2 --Z.sub.2 --, --Z.sub.1 --CH.dbd.CH--Z.sub.1 -- or --CH.dbd.CH--CH.dbd.CH--, each unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio, n is 0 or 1 steht, Y.sub.1 and Y.sub.2 are each independently of the other --S-- or --Se--, Z.sub.1 is --S-- or --Se--, Z.sub.2 is --O--, --S-- or --Se--, Z is --S--, --Se-- or NR.sub.7, and R.sub.7 is H, C.sub.1 -C.sub.6 alkyl, phenyl or benzyl, and R.sub.6 is H, C.sub.1 -C.sub.4 alkyl, phenyl or benzyl;
- or B is the monovalent radical cation of an N-aromatic compound containing a total of 1 to 5 unsubstituted or halogen-, C.sub.1 -C.sub.4 alkyl-- or C.sub.1 -C.sub.4 alkoxy-substituted aromatic rings, at least one of which rings contains at least one --NR.sub.8 -- or [.dbd.N.sup.+ R.sub.8 --] I.sup.- group, wherein R.sub.8 is C.sub.1 -C.sub.4 alkyl or benzyl;
- or
- c) p and q are 2 and
- B is a radical cation of an N-aromatic compound as defined above;
- or
- d) p is 2 and q is 1 and
- B is unsubstituted ferrocene or Fe(indenyl).sub.2 or ferrocene or Fe(indenyl).sub.2 which are substituted by C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 hydroxyalkyl, amino-C.sub.1 -C.sub.6 alkyl, primary or secondary amino-C.sub.1 -C.sub.6 alkyl containing 1 to 12 carbon atoms in the primary amino group and 2 to 12 carbon atoms in the secondary amino group, NH.sub.2, primary amino containing 1 to 12 carbon atoms, or secondary amino containing 2 to 12 carbon atoms.
Dependencies are inferred from the claim text.